diff --git a/src/services/chat/matrix/token-refresher.ts b/src/services/chat/matrix/token-refresher.ts
index e4c272e..2a61c07 100644
--- a/src/services/chat/matrix/token-refresher.ts
+++ b/src/services/chat/matrix/token-refresher.ts
@@ -2,7 +2,10 @@ import type { BrowserContext } from 'playwright';
 import type { Logger } from '../../../utils/logger.js';
 import type { TokenRefresher } from '../service.js';
 import type { MatrixCredentials } from './types.js';
-import { extractMatrixCredentials } from './token-extractor.js';
+import {
+  extractMatrixCredentials,
+  MatrixBrowserLoginRequiredError,
+} from './token-extractor.js';
 
 export interface MatrixSessionBrowser {
   getContext(): BrowserContext | null;
@@ -50,12 +53,10 @@ export class MatrixTokenRefresher implements TokenRefresher {
 
   private async performRefresh(): Promise<void> {
     const sessionValid = await this.browser.isSessionValid();
+    let sessionRestored = false;
     if (!sessionValid) {
-      this.logger.warn('[matrix] Reddit browser session expired; attempting login recovery');
-      if (!(await this.browser.login())) {
-        throw new MatrixRemoteLoginRequiredError();
-      }
-      this.logger.info('[matrix] Reddit browser session restored');
+      await this.restoreSession();
+      sessionRestored = true;
     }
 
     const context = this.browser.getContext();
@@ -63,7 +64,34 @@ export class MatrixTokenRefresher implements TokenRefresher {
       throw new Error('Matrix token refresh requires an initialized browser context');
     }
 
-    const credentials = await this.extract(context, this.logger);
+    let credentials: MatrixCredentials;
+    try {
+      credentials = await this.extract(context, this.logger);
+    } catch (error) {
+      if (!(error instanceof MatrixBrowserLoginRequiredError)) throw error;
+      if (sessionRestored) throw new MatrixRemoteLoginRequiredError();
+
+      this.logger.warn(
+        '[matrix] Reddit API session looked valid but chat requires login; attempting recovery',
+      );
+      await this.restoreSession();
+      try {
+        credentials = await this.extract(context, this.logger);
+      } catch (retryError) {
+        if (retryError instanceof MatrixBrowserLoginRequiredError) {
+          throw new MatrixRemoteLoginRequiredError();
+        }
+        throw retryError;
+      }
+    }
     this.applyCredentials(credentials);
   }
+
+  private async restoreSession(): Promise<void> {
+    this.logger.warn('[matrix] Reddit browser session expired; attempting login recovery');
+    if (!(await this.browser.login())) {
+      throw new MatrixRemoteLoginRequiredError();
+    }
+    this.logger.info('[matrix] Reddit browser session restored');
+  }
 }
diff --git a/tests/matrix-token-refresher.test.ts b/tests/matrix-token-refresher.test.ts
index 91426f7..c6b4eb9 100644
--- a/tests/matrix-token-refresher.test.ts
+++ b/tests/matrix-token-refresher.test.ts
@@ -5,6 +5,7 @@ import {
   MatrixRemoteLoginRequiredError,
   MatrixTokenRefresher,
 } from '../src/services/chat/matrix/token-refresher.js';
+import { MatrixBrowserLoginRequiredError } from '../src/services/chat/matrix/token-extractor.js';
 import type { MatrixCredentials } from '../src/services/chat/matrix/types.js';
 
 const credentials: MatrixCredentials = {
@@ -75,4 +76,23 @@ describe('MatrixTokenRefresher', () => {
 
     expect(applyCredentials).toHaveBeenCalledOnce();
   });
+
+  it('repairs and retries when chat redirects to login despite a valid Reddit API session', async () => {
+    const { refresher, browser, context, extract, applyCredentials } = setup({
+      sessionValid: true,
+      loginSucceeds: true,
+    });
+    extract
+      .mockRejectedValueOnce(
+        new MatrixBrowserLoginRequiredError('https://www.reddit.com/login/?dest=/chat/'),
+      )
+      .mockResolvedValueOnce(credentials);
+
+    await refresher.refresh();
+
+    expect(browser.login).toHaveBeenCalledOnce();
+    expect(extract).toHaveBeenCalledTimes(2);
+    expect(extract).toHaveBeenNthCalledWith(2, context, expect.anything());
+    expect(applyCredentials).toHaveBeenCalledWith(credentials);
+  });
 });